Ultimate 5 Day Maui Itinerary For a Perfect Trip In 2025

Searching for the Perfect 5-Day Maui Itinerary?

Planning a trip to Maui but feeling overwhelmed by all the options? Our 5 day Maui itinerary makes it simple.

From stunning beaches to lush hikes, you’ll know how to spend your time. There is no guesswork, just pure island adventure.

Our family has visited Maui every year for nearly 20 years. In this post, we share our favorite spots on the island. You’ll find must-sees for first-timers and hidden gems for the adventurous. Use this 5 day Maui itinerary to plan an unforgettable trip to the “Valley Isle.”

Affiliate Disclaimer: Some links on this blog are affiliate links. This means that, at no additional cost, the author may earn a small commission if you purchase through these links. As an Amazon Associate, I earn from qualifying purchases.

Essential Maui Travel Tips for Your Journey

It is important to cover the basics before starting our first full day in Maui. After arriving at the airport, we typically stop at Costco or Safeway to purchase weekly provisions. These include snacks, water, soft drinks, and liquor for our villa.

CT Tip: Be sure to swing by the gift card section at Costco! You’ll often find deals on local restaurants and activities, like a sunset sail. Snagging a gift card can save you money while adding some extra fun to your plans.

Additionally, we arrange to rent beach chairs, an umbrella, a cooler, and a wagon for our stay. Are there kids in our group who want to try boogie or paddle boarding? Rentals are available for those as well.

We rent our beach equipment from Auntie Snorkel Lahaina. The equipment is in like-new condition, and their customer service is fantastic.

If we don’t have snorkel gear, we rent it from Auntie Snorkel on our first day to enjoy it throughout our trip. By taking care of all these details upon arrival, we can hit the ground running on our first full vacation day and explore all that Maui offers.

Looking for a snorkeling checklist? Don’t miss our blog post on essential snorkeling gear!

Capture Memories: Book a Flytographer for Stunning Sunset Photos

Booking a Flytographer session in Maui lets you capture your memories with gorgeous professional photos during sunset.

Choose a scenic spot like Wailea Beach or Kapalua Bay for the best background.

Your photographer will guide you on poses to ensure you look your best in every shot. These sessions usually take around an hour, providing numerous photos to remember your trip.

You’ll get the high-quality finished photos within a few days, perfect for sharing and framing. It’s a unique way to remember your Maui vacation forever.

Lahaina and Upcountry Kula had devastating fires on August 8, 2023. Maui is accepting visitors; be prepared for a different West Maui. Please plan ahead and be kind. All of the activities and restaurants listed here are open for business.

Love music and have Wednesday night available?

There is a Slack Key show at the Napili Kai Beach Resort on Wednesday evenings. Doors open at 5:45, and the show is from 6:30 to 8:30. Reserved seats (first four rows) are $60, and General admission is $40.

This show is one of a kind, and if you want to immerse yourself in Hawaiian Culture, this is the place! Four-time Grammy winner George Kahumoku Jr. hosts this weekly show. They often have other guest Hawaiian musicians playing traditional Hawaiian music during the show.

Day 1: Kickstart Your Maui Adventure in West Maui

Breakfast at the Gazebo

Get an early start to enjoy a delicious breakfast at the Gazebo. Although seating is limited, the experience is worth the wait. If the line extends to the top of the steps, expect to wait around 45 minutes before being seated.

A must-try dish is the Macadamia Nut Banana pancakes, accompanied by a serving of fried rice. The fried rice is so good it will leave you longing for more even after leaving Maui. Consider ordering a large portion of fried rice to bring back to your villa as a side dish when grilling fish.

Snorkeling at Honolua Bay

If you are staying on the Ka’anapali side of the island, Honolua Bay is an excellent spot for snorkeling. It’s not your typical beach but rather a destination for underwater exploration.

A .6-mile roundtrip access trail takes you through a lush forest with hanging vines and primarily flat trails to get there.

The bay has a rocky shoreline, so bring water shoes if you have delicate feet. When you first enter the water, visibility may not be ideal but don’t worry – keep going. Head towards the right side of the bay, and you’ll come across a beautiful coral reef.

Keep an eye out for turtles, as they’re often spotted here. We love snorkeling at Honolua Bay and highly recommend it as a must-visit spot.

If you want to visit Honolua Bay and would prefer a boat trip instead of entering from shore, consider booking this West Maui snorkel trip from Ka’anapali.

Pick up Lunch at The Fish Market Maui

If you’re staying at a villa with a grill, check out The Fish Market Maui. It’s our go-to spot for picking up fresh fish to grill.

We always ask for their freshest catch, and they’re happy to give us tips on preparing it. They also have a selection of spices available for purchase. Don’t forget to try their delicious crab cakes – my favorite!

Suppose grilling is not an option, or you prefer to avoid cooking during your vacation. In that case, a relaxed eatery with limited seating is available, or you can opt for takeout instead.

Grab a Poke Bowl from Napili Market as an alternative

Do you enjoy Poke? If so, consider getting your Poke fix from Napilii Market.

This spot is popular among locals for its delicious poke at a very reasonable price. I recommend the Spicy or Hawaiian Poke; if you can’t decide, you could always choose a combination.

If some people in your group are not Poke fans, don’t worry – Joey’s Kitchen and Mama’s Ribs & Rotisserie are in the same shopping complex.

Relax on the Beach after Lunch

Are you looking for a great spot to spend your afternoon? Kapalua Bay Beach and Airport Beach are both excellent choices. Not only do they offer stunning white sand, but they’re also perfect for snorkeling.

Remember to bring your beach chairs, umbrella, and snorkel gear to enjoy these magnificent beaches fully.

During our stays at the Westin Kaanapali Ocean Resort North, we enjoy the fantastic snorkeling opportunities right before the villas, extending to Airport Beach.

We feel fortunate to have easy access to such stunning sealife and a gorgeous beach without having to venture too far.

Enjoy the beautiful Maui Sunset.

Take a moment to unwind on the sandy shores of Maui and witness the breathtaking sunset. Watch for a stunning green flash as the sun dips below the horizon. It’s sure to be a sunset you’ll never forget.

Have Dinner at Monkeypod

If you’re looking for a great dinner spot, I highly recommend checking out MonkeyPod at Whaler’s Village. They make some of the best Mai Tais on the island, and their No Ka ‘Oi drink is also our favorite.

Trust me, you won’t want to miss out on trying the Pumpkin Patch ravioli—it’s not a typical Maui dish, but it’s incredible. The Truffle Oil Garlic fries are another must-try appetizer. We recommend the delicious Hamakua Wild Mushroom and Truffle Oil Pizza for your main course.

The Banana or Strawberry cream pie is delicious, so save room for dessert! Monkeypod is one of our favorite Maui restaurants, and we usually visit multiple times during our stays.

Day 2: Explore Maui’s Upcountry

Discover the Wonder of Haleakala National Park

Explore the marvels of Haleakala National Park, where you can immerse yourself in the breathtaking vistas of the Haleakala Crater, experience a sunrise or sunset that will leave you in awe, and set off on a picturesque hike through its stunning landscapes.

Haleakala is a must-visit when planning your 5 day Maui itinerary. The landscape is as if you have landed on another planet.

If catching the sunrise at Haleakala is a must-do, we suggest swapping Day 1 with Day 2 to allow you to take advantage of the time difference.

Planning a sunrise visit? Be sure to purchase your tickets ahead of time! Tickets on the recreation site can be reserved up to 60 days in advance but no later than 2 days before your visit.

Sunrise entry is from 3:00 to 7:00 am and costs just $1 per car, plus the National Park Service fee of $30 per vehicle. After 7:00 am, no reservations are needed to enter the park.

Planning to visit the Pipiwai Trail? Be sure to go within three days of your Haleakalā visit, as the entrance fee is valid for 72 hours.

If you choose to do sunrise but don’t want to drive it, consider doing this tour: Haleakala Sunrise tour with Breakfast. Another fun and very popular option is biking in Haleakala. If you choose to do the biking tour, be cautious, and we don’t recommend it if you haven’t ridden a bike in years.

After viewing the sunrise, head over to the Kula Lodge for a hearty breakfast.

We prefer to ease into our Maui vacation and suggest saving this activity for Day 2. If you plan to explore the park during the day or catch the sunset, there’s no need to worry about purchasing park tickets ahead of time.

Bring a jacket and dress appropriately, as it is much colder at the summit.

Explore the Upcountry of Maui.  There are so many options for exploring, depending on your interest.

Explore the Kula Botanical Gardens.

If you’re looking for a breathtaking and serene place to explore in Maui, the Kula Botanical Gardens must be on your list.

Situated on the slopes of Haleakala, this 8-acre garden is filled with various tropical flora worth visiting. From orchids and bromeliads to native trees and succulents, the Kula Botanical Gardens have a diverse range of plants that will give you an appreciation for Maui’s natural beauty.

The garden offers stunning views of the island and the Pacific Ocean, making it an excellent photo-op spot.

Tour a local farm such as the Ali’I Kula Lavender Farm or O’o Farm

If you’re looking for a unique and authentic experience on Maui, consider touring a local farm like Ali’i Kula Lavender Farm or O’o Farm. Both farms offer guided tours that allow you to explore their beautiful grounds and learn about sustainable farming practices.

At Ali’i Kula, you’ll be surrounded by acres of lavender fields and may even be lucky to glimpse their resident peacocks roaming about. Meanwhile, O’o Farm offers a hands-on experience where you can pick organic produce from the garden and enjoy a farm-to-table lunch.

Whichever farm you visit, you will see a different side of Maui and support local agriculture. Don’t miss out on this unique opportunity to connect with nature and learn about the local farming industry.

Upcountry Lunch Options

There are many options for eating upcountry on Maui. However, if you’re looking for a meal with a view and a taste of local flavor, consider stopping at the O’o farm, Ulupalakua Ranch Store Grill, Kula Bistro, or Hali’imaile General Store for lunch.

Each venue offers a personalized experience that showcases different aspects of the island. At the O’o farm, you can indulge in a farm-to-table lunch experience surrounded by lush greenery and stunning views.

At the same time, Ulupalakua Ranch Store Grill serves unique juicy burgers and sandwiches alongside its famed Maui views.

Kula Bistro offers a bakery with delightful desserts and large-portion dishes that emphasize the unique flavors of the island, and Hali’imaile General Store serves Hawaiian comfort food elevated with a modern twist.

Each spot offers a unique look at what makes Maui’s food and drink scene so special.

Maui Wine Tasting Room and its’ picturesque vineyard, Ulupalakua ranch

If you are looking for a unique tasting experience on Maui, look no further than Maui Wine‘s tasting room. The picturesque Ulupalakua Ranch vineyard offers stunning views of the verdant rolling hills and is the perfect place to sit and relax with a glass of wine.

The winery produces various wines, including pineapple wine, which is not to be missed. Take a vineyard tour and learn about the ranch’s history and how the wines are made.

Whether you’re a wine lover or just looking for something fun and different to do on Maui, the Maui Wine tasting room is worth a visit.

Sunset at Ocean Vodka

If you plan on spending the whole day experiencing Upcountry, consider visiting Ocean Vodka at the end of your day. They have a picturesque setting where you can enjoy the sunset.

Their spacious lawn has picnic tables and Adirondack chairs, perfect for a casual outing to view the sunset. Enjoy the live music with their delicious menu and craft cocktails.

Ocean Vodka has breathtaking views with the sunset over the West Maui Mountains. which is truly spectacular.

Hike the Polipoli Spring State Recreation Area

If you’re looking for a unique way to experience Maui’s natural beauty, you won’t miss the chance to hike the Polipoli Spring State Recreation Area. Located in Upcountry Maui, this hidden gem boasts stunning panoramic views of the island, including the neighboring islands of Lanai and Molokai.

As you trek through the lush forests and explore the volcanic landscapes, you’ll encounter an array of native flora and fauna, including towering evergreens and colorful wildflowers.

Whether you’re an experienced hiker or just looking for a stroll with family and friends, this is a must-see destination on your list of what to see on Maui.

Consider taking this Private Upcountry tour, which is an 8-hour tour of Upcountry, including Kula and Makawao.

Makawao for its local art galleries, shops, and restaurants.

If you’re looking for a charming town to visit in Maui, Makawao should be at the top of your list. With its quaint streets lined with local art galleries, unique shops, and delicious restaurants,

Makawao offers visitors a taste of the island beyond typical tourist attractions. Whether you’re interested in perusing local artwork, shopping for one-of-a-kind items, or indulging in some mouth-watering cuisine, Makawao has something for everyone.

Surfing Goat Dairy for some goat cheese

If you’re a goat cheese lover and are visiting Maui, visiting Surfing Goat Dairy is a must. Located in beautiful upcountry Maui, this family-owned dairy farm has produced some of the freshest and tastiest goat cheese for over a decade.

Take a farm tour and meet the friendly goats who call this place home. Watch the cheesemakers create signature flavors like mango, garlic, and truffle. After your tour, sample some delicious goat cheese and purchase some as a tasty souvenir. A visit to Surfing Goat Dairy is a unique and delicious addition to any Maui itinerary.

Consider booking this Private Farm Tour, a private tour of three upcountry farms.

Are you feeling tired? Upcountry offers many activities that are difficult to fit into just one day. Despite visiting Maui annually for almost 20 years, we are continually amazed by the new restaurants and activities we discover. This is one of the many reasons we adore Maui so much.

Day 3: Dive into What Makes Maui Unique

Whale Watching or Snorkel Trip

If you are visiting between December and April, schedule a whale-watching trip. This is one of the main reasons we love to travel to Maui in February and March. These magnificent animals come to the warm, shallow waters to breed and birth their babies.

There are many options for whale-watching tours. Depending on your interests, you can combine the tour with snorkeling or just whale watching. We highly recommend Captain Steve’s Rafting for a whale-watching tour. Since the Lahaina Fire, they have partnered with Hawaii Ocean Rafting and Makai Adventures for their tours. Please support these local businesses’ rebuilding.

If you are not traveling during Whale Season, we recommend Captain Steve’s Rafting snorkel tour or a Molokini Snorkel trip. Our personal preference is to snorkel Lanai.

There are so many excellent restaurants in the Lahaina area. I have an entire blog post for Best Breakfast in Lahaina & Ka’anapali, Maui, and Best Ka’anapali Restaurants for Ocean View Dining Guide 2024

Lunch at Whaler’s Village

After a morning on the ocean, head to Whaler’s Village for lunch. Several great restaurants exist at Whaler’s Village, such as Hula Grill or Leilani’s, which are great for an ocean view. Joey’s Kitchen and Maui Poke are on the lower level for something casual.

After lunch, walk around Whaler’s Village to shop for souvenirs.

Have Shave Ice for Dessert

Do you want dessert after lunch? Try shave ice at Ululani’s Hawaiian Shave Ice.

There are several Ululani’s Shave Ice shops around the Island. I highly recommend trying a shave ice from Ululani’s before you leave Maui.

After a satisfying lunch, a dessert is the perfect way to finish it.

Ululani’s has been voted the best shave ice on the island for years. They use premium syrups and real fruit purees to make their fluffy shave ice. My personal favorite Ululani’s treat is Sunset Beach shave ice over Macadamia Nut Ice Cream and a snowcap topper.

Experience a Traditional Hawaiian Luau

When looking for something to see on Maui, there’s nothing quite like experiencing a luau. The Old Lahaina Luau offers a whole evening of entertainment, traditional Hawaiian cuisine, and unforgettable cultural experiences.

At the Old Lahaina Luau, you’ll begin with a lei greeting and be transported back to when islanders gathered for special events. Each meal course, from kalua pork to haupia pudding, is expertly prepared and served with hula dancers and live music, with the ocean as the backdrop.

There are many other options for luaus on Maui, depending on your price range and where you stay. Another great choice is the Maui Nui Luau at the Sheraton Resort.

Day 4: Continue Your Maui Exploration on the Road to Hana

Discover the beauty of the Road to Hana

Embark on a thrilling journey along the scenic drive of the Hana Highway—the Road to Hana is where you’ll discover breathtaking waterfalls and lush rainforests. With so many sights to see, it’s hard to cover everything in detail.

Be warned, if you stop at every recommended location, you may not make it to Hana before nightfall. My post on the Road to Hana has the must-stop locations for a perfect day trip.

To enhance your road trip, use the Maui Revealed book and the Shaka app, which offers an audio tour of the Road to Hana; we prefer to drive to our must-see stops and then stop whatever we have time for on the way back to Lahaina.

For a delicious lunch, we recommend visiting Thai Food from Pranee. Another favorite place that we like to stop for lunch is Huli Huli Chicken. We happened upon this open-air stand off the Road to Hana over a decade ago, and it’s been a must-stop for us ever since. In Hana, there is a food truck lot with various options.

If you plan to visit the Honokalani Black Sand Beach, reservations are required to enter Waianapanapa State Park.

Visit Ho’okipa Beach to see Turtles.

If you plan a trip to Maui, you won’t want to miss Ho’okipa Beach. This little gem is a great place to see sea turtles sunbathing on the shore, and the views are stunning.

It’s the perfect spot to stop after a long day of exploring the Road to Hana or at the start of your journey to soak in the island’s beauty.

You might even glimpse some windsurfers or surfers riding the waves if you’re lucky.

Are you not interested in doing the drive yourself?  I don’t blame you; the roads are narrow and winding. Being a passenger and taking in the gorgeous sights is much easier. Click here for the Best Road to Hana tour.

Plan on Dinner in Paia

If you’ve spent a long day traveling the Road to Hana, I highly suggest grabbing dinner at Paia Fish Market or the Flatbread Company.

Are you looking to experience Maui’s charm while indulging in some retail therapy? Look no further than Paia!

This picturesque town perfectly blends souvenir shopping and stunning Hawaiian artwork displays. Whether you’re in the mood for leisurely window shopping or eager to find that perfect gift for someone special, Paia is a must-visit destination.

Mama’s Fish Market is my top recommendation for those seeking a more upscale dining experience in the area. Having traveled extensively and dined at many exceptional restaurants, Mama’s is truly the best. However, make reservations well in advance – I’ve already secured ours nine months in advance.

You may be tempted to fill up on their delicious homemade bread, but save room for your entree. I highly recommend the Hawaiian Kanpachi with crab and lobster in a Macadamia Nut Crust. It’s amazing! If you want an appetizer, I recommend the Haleakala Beef in a mango bowl or the Macadamia Nut Crab Cakes.

Day 5: Spend Your Last Day in South Maui

Start with a hearty breakfast from Nalu’s South Shore Grill in Kihei

When starting your day in Kihei, you can’t go wrong with breakfast at Nalu’s South Shore Grill. This cozy cafe offers a delightful array of breakfast dishes that will leave you satisfied and ready to take on whatever your day holds.

From fluffy banana nut pancakes to their fabulous loco moco, there is something for everyone on the menu. Nalu’s is located in the heart of Kihei, making it a great pit stop before exploring all the fantastic sights and attractions South Maui offers.

Explore Makena State Park

Regarding what to see on Maui, the sea turtles at Makena Beach should be on your list. There’s something truly awe-inspiring about watching these gentle giants spend their sweet time lounging on the golden sand. You can’t help but feel a sense of privilege and respect as you observe them in their habitat.

And even better, the crystal clear waters of Makena provide a great opportunity for you to join these majestic creatures in their natural habitat for a swim or snorkel, provided you keep a respectful distance, of course!

Makena Beach is 1.5 miles long and 100 yards wide and has gorgeous fine white sand. Because of its size, it usually doesn’t feel overcrowded. It is part of Makena State Park. Little Beach is just North of Big Beach. It is much smaller, 660 feet long, and more secluded but crowded. Little Beach is also known as Pu’u Olai Beach.

Another beach part of the Makena State Park is the black sand beach, One’uli, also known as Naupaka Beach. The unique black sand is made of lava rock, unlike typical beach sand made of ground coral and shells.

Ocean Kayaking and snorkeling

Are you looking for an adventure more exciting than just lounging on the beach? Consider going on an ocean kayaking trip. This stunning and unspoiled coastline is home to Hawaiian green sea turtles, and kayaking is an excellent way to get a close-up view of these gentle giants.

Watch for schools of tropical fish and colorful coral reefs as you paddle through the crystal-clear waters. It’s a breathtaking sight that makes you feel like floating in an underwater paradise.

Whether you’re an experienced kayaker or a first-timer, this adventure is informative and interactive, so add it to your 5 day Maui itinerary. It’s a unique experience that will create memories that will stay with you forever.

Lunch near Kihei at Maui Brewing Company

There are many options for grabbing lunch in South Maui, but one spot that shouldn’t be missed is Maui Brewery in Kihei. Not only do they serve delicious burgers and fries, but their selection of craft beers is top-notch.

Plus, the atmosphere is always fun and laid-back. Maui Brewery offers a rotating selection of house-made beers, such as their popular Bikini Blonde Lager and Big Swell IPA. Don’t forget to ask your server for recommendations on which beer will pair best with your meal.

But if you’re looking for a quick and tasty bite with some great local flavor, Coconuts in Kihei is a great spot. With an expansive menu ranging from poke bowls to fish tacos, there’s something for everyone.

The outdoor seating area is also perfect for soaking up some sun while you eat. Maui Brewery and Coconuts offer a taste of the island you won’t want to miss.

Another excellent choice with a great fish selection is the Paia Fish Company. It is one of our favorites. On every trip, we are sure to dine there at either location, Paia or Kihei

End your 5 days on Maui with an unforgettable sunset cruise

As your Maui vacation draws close, there’s no better way to bid farewell than with a sunset sail across the ocean. Sea Maui offers some of the best sunset cruises on the island.

As you sail in the distance, you’ll be treated to breathtaking views of Maui’s stunning coastline and the colors only a sunset on Maui can provide.

Take in the fresh ocean breeze, unwind, and let the beauty of Maui surround you. It’s the perfect way to end your trip and create unforgettable memories that will stay with you long after you return home.

The best time to Visit Maui

When’s the best time to visit Maui? Honestly, there’s never a bad time!

Maui’s tropical climate means warm weather year-round, depending on what kind of vibe you’re after. If you’re chasing humpback whales, plan your trip between December and March when these gentle giants migrate through.

If you’ve been following us for a while, you already know Whale Season is our favorite time to visit Maui. No matter how many years we’ve been coming, watching those majestic humpback whales with their babies never gets old!

Want fewer crowds and better deals? Go during the shoulder seasons, April-May or September-October, when the island feels slightly laid-back.

And if you’re dreaming of endless sunny beach days, the summer months (June-August) are your time to shine. No matter when you go, Maui will steal your heart!

Let’s talk Maui weather!

This beautiful island’s climate is as varied as its stunning landscapes. The leeward side (think Lahaina, Kihei, and Wailea) is your go-to for sunshine and warm, dry days—perfect for beach bumming.

Meanwhile, the windward side (like Hana and the lush road leading there) gets more rain, keeping those waterfalls and rainforests thriving.

Temperatures usually hover between 75°F and 85°F year-round, but bring a jacket if you’re heading up to Haleakalā—the summit can drop to a chilly 40°F!

Getting Around Maui

To truly soak in the beauty of Maui, we highly recommend renting a car. It’s the best way to explore the island at your own pace—stop for those jaw-dropping views, hunt down hidden beaches, and take your time along the famous Road to Hana.

Public transportation and ride-sharing? They’re pretty limited here, so you won’t want to rely on them if you plan to see more than your hotel pool or nearby beach.

Not a fan of driving? No worries! Many tours include hotel pick-up, so you can still get to all the must-see spots hassle-free.

Adventure awaits whether you’re cruising in a rental car or hopping on a tour bus!

What reservations that are needed in advance

• Haleakala National Park
• Iao Valley State Park
• Wai’anapanapa State Park
• Mama’s Fish House = over 6 months in advance
• Luau, especially Old Lahaina Luau
• Ocean Vodka tour

For most Maui restaurants, you must make reservations for around 1-2 months before. Places like Star Noodle, Aloha Mixed Plate, Mala, Merriman’s, Sansei, and Monkeypod need reservations. If you are set on those restaurants, plan ahead.

If your itinerary is tight and there are must-do activities such as snorkeling, sunset sailing, or whale watching, you will want to book in advance. We usually wait to book our sunset sailing until we check out what Costco has, but our schedule is flexible after visiting every year.

What to Pack for Your Maui Adventure

Packing for Maui is about staying comfy, stylish, and ready for adventure!

If you love snorkeling and have your own gear, bring it along. Don’t forget reef-safe sunscreen, a sun hat, and activewear if hiking is on your itinerary. Waterproof hiking sandals or boots are a must for those trails (or slippery waterfall spots).

Beach essentials? Think of a roomy beach bag, sunglasses, and sturdy beach shoes. If you’re into capturing those epic moments, a GoPro or underwater camera is perfect—don’t forget a float strap to keep it safe in the water!

Bring several swimsuits and cover-ups because, let’s face it, you’ll practically live in them. During the day, casual clothes like tank tops, shorts, and breezy outfits are perfect for layering over your swimwear.

For dinner, Maui’s vibe is relaxed yet classy. Ladies, pack sundresses or flowy skirts paired with cute sandals. Guys, opt for a collared short-sleeve shirt (polo or Aloha style) with dress shorts or khakis and finish the look with closed-toe shoes for finer restaurants.

It’s all about casual resort wear with a touch of island flair. Check out our post on packing for Maui for more in-depth information on what to bring.

Top Restaurant Recommendations for Maui

Breakfast Spots

• Gazebo Restaurant at Napili Shores
• Castaway Cafe Lahaina
• Nalu’s South Shore Grill Kihei
• Duke’s Beach House Ka’anapali
• Aloha Mixed Plate Lahaina
• Kula Lodge & Restaurant
• Sea House Napili

Casual Dining

• The Fish Market Lahaina
• Coconuts Kihei
• Tin Roof Kahului
• Burger Shack Kapalua
• Like Poke? Food Truck & Kahului
• Maui Brewing Company Kihei or Ka’anapali
• Paia Fish Market Paia or Kihei

Evening Dining

• Monkeypod Ka’anapali & Waliea
• Mama’s Fish House Paia
• Hula Grill Ka’anapali
• Star Noodle Lahaina
• Sansei Kapalua
• Merriman’s Kapalua
• Mala Ocean Tavern Lahaina
• Tiffany’s Bar & Grill Wailuku

Sweet Treats

• Leoda’s Kitchen & Pies Lahaina
• Ululani’s Shave Ice Kihei
• Lorraine’s Shave Ice & Banana Bread
• Hula Pie (Duke’s, Leilani’s, Hula Grill)
• Strawberry Pie from Monekypod

Check out our Best Restaurants in West Maui blog post for a more in-depth review.

Where to Stay on Maui

Regarding where to stay in Maui, you’ve got two main areas to choose from: South Maui and West Maui. Each has its unique vibe, so it depends on what kind of trip you’re looking for!

South Maui (Wailea & Kihei)

Wailea is your spot if you’re after luxury. This area is home to some of the island’s most stunning high-end resorts, perfect for indulging in a bit of island glamour.

Just a short drive away, Kihei offers a more laid-back vibe with plenty of condo rentals, making it a great choice if you’re looking for something more budget-friendly but still close to the action.

Both areas are sunny and have beautiful beaches, so no matter where you stay, you’ll be soaking up the good Maui vibes.

Recommended South Maui Hotels

• Sugar Beach Resort, Kihei – Best Chocie
• Wailea Grand Champions, Wailea – Best Value
• Grand Wailea, Wailea – Luxury

West Maui (Kaanapali, Napili, and Kapalua)

If you want to know our preference, it’s West Maui! More particularly, Ka’anapali.

Ka’anapali has plenty of resorts, which is perfect for those who want a full resort experience with many amenities.

Napili is quieter, with boutique hotels and condos right by the beach, giving you a more intimate, low-key atmosphere.

And if you’re in the mood for luxury again, Kapalua’s high-end resorts are perfect for those looking for a peaceful, upscale getaway with world-class golf.

Maui’s beauty will surround you no matter where you stay, but West Maui’s charm holds a special place in our hearts!

Recommended West Maui Hotels

• Westin Ka’anapali Ocean Resort Villas, Ka’anapali – Best Choice
• Napili Shores Maui by Outrigger, Napili – Best Value
• Montage Kapalua Bay, Kapalua – Luxury

Final Thoughts: Making the Most of Your 5 Day Maui Itinerary

In conclusion, a 5 day Maui travel itinerary is the perfect way to experience all that this breathtaking island has to offer. From driving along the stunning Road to Hana to exploring the scenic Upcountry and witnessing the majestic Haleakala, your days will be filled with adventure and wonder.

And what better way to top off your stay in Maui than attending a traditional Luau, where you can immerse yourself in the rich Hawaiian culture and cuisine? It’s safe to say that these are just some of our top choices for an unforgettable trip to Maui.

Have more time on Maui than five days? Check out our 10-Day Maui Itinerary

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Grab Life & Don’t Forget To Wear Sunscreen! Happy Exploring!

5 Day Maui Itinerary: FAQ

Our Trusted Resources

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Booking.com: for booking accommodations

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